Spray a 9" springform pan with cooking spray, then gently blot the cooking spray with a paper towel. In a large bowl, combine the Oreo crumbs and the melted butter until moistened. Press into the prepared springform pan to form a crust, and work the crumb crust up the sides of the pan. Set aside.
In the bowl of a stand mixer, cream the cream cheese on medium-high speed for 2-3 minutes, or until it's light and fluffy. Add in the sugar and combine. Next, add in the heavy cream and vanilla extract. Slowly add in the dry brownie mix, beating on medium speed until the dry mixture is completely incorporated into the cheesecake mixture. Pour the filling into the prepared pan and smooth out the top gently. Refrigerate for 4 hours.
To make the glaze, in a small bowl whisk together the dry brownie mix, oil and heavy cream until smooth. For a slightly thinner glaze, add additional heavy cream. Drizzle the glaze over the cheesecake and/or on the plates before plating the cheesecake.
To make the whipped cream, beat the heavy cream and powdered sugar on high speed for 5-7 minutes or until stiff peaks form. Pipe onto the cheesecake in a decorative design around the edge of the cheesecake, or serve alongside the cheesecake.